GB971669A - 4-phosphorinanone derivatives and methods of preparing same - Google Patents
4-phosphorinanone derivatives and methods of preparing sameInfo
- Publication number
- GB971669A GB971669A GB40661/62A GB4066162A GB971669A GB 971669 A GB971669 A GB 971669A GB 40661/62 A GB40661/62 A GB 40661/62A GB 4066162 A GB4066162 A GB 4066162A GB 971669 A GB971669 A GB 971669A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phosphorinanone
- alkyl
- compound
- carbon atoms
- reacting
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- GVFQLFXNYFKVCA-UHFFFAOYSA-N phosphinan-4-one Chemical class O=C1CCPCC1 GVFQLFXNYFKVCA-UHFFFAOYSA-N 0.000 title abstract 6
- 125000004432 carbon atom Chemical group C* 0.000 abstract 6
- -1 chloro-substituted phenyl Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000003254 gasoline additive Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000012299 nitrogen atmosphere Substances 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 abstract 1
- 229940126062 Compound A Drugs 0.000 abstract 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 150000002923 oximes Chemical class 0.000 abstract 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 abstract 1
- 229940067157 phenylhydrazine Drugs 0.000 abstract 1
- ALQHHUFONRFGMF-UHFFFAOYSA-N phosphinan-2-one Chemical class O=C1CCCCP1 ALQHHUFONRFGMF-UHFFFAOYSA-N 0.000 abstract 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 abstract 1
- 150000007659 semicarbazones Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
- C07F9/65688—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphonium compound
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
- C07F9/65683—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
- C07F9/65685—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine oxide or thioxide
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/26—Organic compounds containing phosphorus
- C10L1/2608—Organic compounds containing phosphorus containing a phosphorus-carbon bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Indole Compounds (AREA)
Abstract
The invention comprises 4-phosphorinanone derivatives of the general formulae <FORM:0971669/C1/1> <FORM:0971669/C1/2> <FORM:0971669/C1/3> <FORM:0971669/C1/4> <FORM:0971669/C1/5> <FORM:0971669/C1/6> wherein R is a substituted or unsubstituted alkyl, having 1 to 18 carbon atoms, cycloalkyl or aryl radical; each of R1, R2, R3 and R4 is a hydrogen atom or an alkyl, phenyl, chloro-substituted phenyl, alkyl-substituted phenyl or alkoxyalkyl radical in all of which the alkyl and alkoxy radicals contain 1 to 6 carbon atoms; each of R5 and R6 is a hydrogen atom or an alkyl radical containing 1 to 6 carbon atoms, R7 is an alkyl radical containing 1 to 12 carbon atoms and X is halogen. The compounds may be prepared from the corresponding 4-phosphorinanone compounds by (1) heating with sulphur at 50 DEG to 150 DEG in the presence of an inert solvent (compound A); (2) reacting with an alkyl halide in a nitrogen atmosphere at 0 DEG to 80 DEG C. (compound B); (3) reacting with semicarbazide hydrochloride in the presence of a weak base and an alkanol, containing 1 to 6 carbon atoms, at 40 to 100 DEG C. (compound C); (4) reacting with a phenylhydrazine in a nitrogen atmosphere and in the presence of an alkanol, containing 1 to 6 carbon atoms, at 50 to 100 DEG C. (compound D); (5) reacting with paranitrophenylhydrazone as in (4) above (compound E) and (6) reacting with hydroxylamine hydrochloride and alkali metal hydroxide at 50 to 100 DEG C. in water (compound F). The compounds of the invention may be used as gasoline additives (see Division C5). Specifications 931,229 and 963,118 are referred to.ALSO:4 - Phosphorinanone - 1 - sulphides; 1 alkyl-4 - oxophosphorinanium halides; 4 - phosphoninanone, semicarbazones; 4 - phosphorinanone, phenylhydrazones; 4 - phosphorinanone, para - nitro - phenylhydrazones; and 4 - phosphorinanone, oximes (see Division C2) are used as gasoline additives to afford protection against misfiring and surface ignition by addition of, for example, 10 mls. of any one of the phosphorinanone derivatives to 1 gallon of gasoline. Specifications 931,229 and 963,118 are referred to.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US161438A US3225103A (en) | 1961-12-22 | 1961-12-22 | 4-phosphorinanone-1-sulfides |
| US485971A US3274246A (en) | 1961-12-22 | 1965-08-09 | Phosphorinanone-phenylhydrazones |
| US485973A US3281463A (en) | 1961-12-22 | 1965-08-09 | Semicarbazones of 4-phosphorinanones |
| US485970A US3316304A (en) | 1961-12-22 | 1965-08-09 | 1-alkyl-4-oxophosphorinanium halides |
| US485972A US3271449A (en) | 1961-12-22 | 1965-08-09 | Phosphorinanone oximes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB971669A true GB971669A (en) | 1964-09-30 |
Family
ID=27538641
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB40661/62A Expired GB971669A (en) | 1961-12-22 | 1962-10-26 | 4-phosphorinanone derivatives and methods of preparing same |
Country Status (2)
| Country | Link |
|---|---|
| US (4) | US3316304A (en) |
| GB (1) | GB971669A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4539421A (en) * | 1983-10-11 | 1985-09-03 | Ciba-Geigy Corporation | 1H-Polyalkyl-phosphorinanes |
| US4642382A (en) * | 1983-10-11 | 1987-02-10 | Ciba-Geigy Corporation | 1H-polyalkyl-phosphorinanes |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL262863A (en) * | 1960-04-06 | 1900-01-01 |
-
1962
- 1962-10-26 GB GB40661/62A patent/GB971669A/en not_active Expired
-
1965
- 1965-08-09 US US485970A patent/US3316304A/en not_active Expired - Lifetime
- 1965-08-09 US US485972A patent/US3271449A/en not_active Expired - Lifetime
- 1965-08-09 US US485973A patent/US3281463A/en not_active Expired - Lifetime
- 1965-08-09 US US485971A patent/US3274246A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4539421A (en) * | 1983-10-11 | 1985-09-03 | Ciba-Geigy Corporation | 1H-Polyalkyl-phosphorinanes |
| US4642382A (en) * | 1983-10-11 | 1987-02-10 | Ciba-Geigy Corporation | 1H-polyalkyl-phosphorinanes |
Also Published As
| Publication number | Publication date |
|---|---|
| US3281463A (en) | 1966-10-25 |
| US3274246A (en) | 1966-09-20 |
| US3271449A (en) | 1966-09-06 |
| US3316304A (en) | 1967-04-25 |
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